Palladium-catalyzed 1,1-aminoxylation of 3-butenoic acid with 2-alkynylanilines

被引:0
|
作者
Zhang, Jinhui [1 ]
Mao, Lihua [1 ]
Liu, Chao [1 ]
Tan, Xiangwen [1 ]
Wu, Jiahao [1 ]
Wei, Xuefeng [1 ]
Wu, Wanqing [1 ]
Jiang, Huanfeng [1 ]
机构
[1] South China Univ Technol, Sch Chem & Chem Engn, Key Lab Funct Mol Engn Guangdong Prov, Guangzhou 510640, Peoples R China
基金
中国国家自然科学基金;
关键词
Musculoskeletal system;
D O I
10.1039/d4cc03099k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Herein, a palladium-catalyzed 1,1-aminoxylation of 3-butenoic acid and 2-alkynylanilines has been developed, achieving the installation of two distinct heteroatom motifs across an olefin skeleton. The strategy features a high step and atom economy and good functional group tolerance, which outlines an efficient approach for simultaneously building up gamma-butylactone and indole skeletons. Notably, an external ligand, 2,9-dimethyl-1,10-phenanthroline, has been used to succeed in this protocol to effectively suppress the production of indole byproducts. A novel palladium-catalyzed 1,1-aminoxylation of 3-butenoic acid with 2-alkynylanilines has been developed.
引用
收藏
页码:9404 / 9407
页数:4
相关论文
共 50 条
  • [1] Palladium-Catalyzed Direct C-H Arylation of 3-Butenoic Acid Derivatives
    Yang, Shan
    Liu, Lingling
    Zhou, Zheng
    Huang, Zhibin
    Zhao, Yingsheng
    ORGANIC LETTERS, 2021, 23 (02) : 296 - 299
  • [2] Synthesis of 3-Chloroindoles via Palladium-Catalyzed Chlorocyclization of Unmasked 2-Alkynylanilines
    Zheng, Yongpeng
    Li, Jianxiao
    Wu, Wanqing
    Qi, Chaorong
    Jiang, Huanfeng
    ADVANCED SYNTHESIS & CATALYSIS, 2025,
  • [3] Palladium-Catalyzed E-Selective Oxidative Amination of Aromatic Amine with 3-Butenoic Acid
    Liu, Qianqian
    Zhou, Zheng
    Huang, Zhibin
    Zhao, Yingsheng
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (21): : 15350 - 15357
  • [4] Palladium-Catalyzed Decarboxylative Coupling of Alkynoic Acids with 2-Alkynylanilines in Ionic Liquid
    Lai, Yin-Long
    Xiong, Xun
    Zhao, Ting
    Li, Jianxiao
    Zhong, Rui-Min
    Xiong, Wenfang
    Jiang, Huanfeng
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2025,
  • [5] Palladium-Catalyzed Annulation of Tertiary Anilines with 3-Butenoic Acid via Dual C-H Bond Activation
    Zhang, Jinhui
    Liu, Chao
    Wu, Jiahao
    Tan, Xiangwen
    Wu, Wanqing
    Jiang, Huanfeng
    ORGANIC LETTERS, 2024, 26 (21) : 4422 - 4426
  • [6] PALLADIUM CATALYZED REACTION OF 2-ALKYNYLANILINES WITH ALLYL CHLORIDES - FORMATION OF 3-ALLYLINDOLES
    IRITANI, K
    MATSUBARA, S
    UTIMOTO, K
    TETRAHEDRON LETTERS, 1988, 29 (15) : 1799 - 1802
  • [7] Palladium-Catalyzed One-Pot Consecutive Amination and Sonogashira Coupling for Selective Synthesis of 2-Alkynylanilines
    Pan, Shanfei
    Ma, Xueji
    Zhong, Danni
    Chen, Wanzhi
    Liu, Miaochang
    Wu, Huayue
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (14-15) : 3052 - 3056
  • [8] Palladium-catalyzed carbonylative cyclization of 2-alkynylanilines and aryl iodides to access N-acyl indoles
    Yao, Lingyun
    Shang, Yan
    Wang, Jian-Shu
    Pan, Ailin
    Ying, Jun
    Wu, Xiao-Feng
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (09): : 1926 - 1929
  • [9] N-Heterocyclic carbene palladium-catalyzed cascade annulation/alkynylation of 2-alkynylanilines with terminal alkynes
    Li, Jianxiao
    Li, Can
    Ouyang, Lu
    Li, Chunsheng
    Wu, Wanqing
    Jiang, Huanfeng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (37) : 7898 - 7908
  • [10] Palladium-Catalyzed Synthesis of Functionalized Indoles by Acylation/Allylation of 2-Alkynylanilines with Three-Membered Rings
    Yuan, Weiliang
    Li, Xiaojiao
    Qi, Zisong
    Li, Xingwei
    ORGANIC LETTERS, 2022, 24 (11) : 2093 - 2098